What’s your biggest maintenance headache on the network – and how are you solving it?

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As far as I’m concerned, one of the things that gives me the biggest headache when it comes to network maintenance, is probably everything related to patch management. Oh, we do have an awesome patch management solution where I work, but the whole thing is still driving me insane occasionally. Patches breaking operating systems, patches not deploying properly, and patches being just plain frustrating. But unfortunately, they’re a necessary evil, and can even be a blessing on occasions.

But what about you, dear IT geeks? What’s your biggest maintenance headache on YOUR network – and how are you solving it?

Outside hack attempts. I've written a few utilities that monitor event viewer, HTTPERR logs, and FTP logs then automatically block ip addresses of machines attempting dictionary attacks and common vulnerability scans. For attempts against our mail server, there's a huge disparage on what it logs to disk versus what it logs on screen and it pretty much locks the log files while in use preventing read access. So every morning I have to manually scan through them to find anything I might need to block. After my scan, I try to report as many to their ISP as possible.

Licensing and product contracts: please, oh PLEASE can't we just use open source software??? Hours and hours on the phone with customer support to get control of the licenses a vendor (Citrix) accidentally assigned to another organization in a completely different city. MONTHS to solve it.

My local coworkers think of me as the IT Guy..and compared to them…I am, but I know I'm not. I know that I know just enough to back the hell away from it and call IT:
Them: "But can't you fix it?"
Me: "No. You downloaded it. you call IT."
Me: …I walk away and surreptitiously send an e-mail to our IT Dept.
Me: "IT X opened the suspicious e-mail they were warned not to open…again."